(S,S)-1,2-di-tert-butylethane-1,2-diamine | 171357-22-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S,S)-1,2-di-tert-butylethane-1,2-diamine
• 英文别名: (1S,2S)-1,2-di-tert-butylethylenediamine；2,2,5,5-tetramethylhexane-3,4-diamine；(3S,4S)-2,2,5,5-tetramethylhexane-3,4-diamine
• CAS: 171357-22-5
• 化学式: C₁₀H₂₄N₂
• 分子量: 172.314
• InChiKey: WROMFDZPVVQJRK-HTQZYQBOSA-N

物化性质

• 沸点：
  217.0±8.0 °C(Predicted)
• 密度：
  0.853±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S,S)-1,2-di-tert-butylethane-1,2-diamine 在 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 19.0h， 生成 (4S,5S)-2-(2-diphenylphosphanylphenyl)-4,5-di-tert-butyl-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  用BIPI配体探索不对称Heck反应中的电子效应。

  摘要：

  [结构：见正文]新的BIPI配体是膦基咪唑啉，可在三个不同的配体区域进行电子调节，以探索不对称催化中的电子效应。描述了它们在手性四元中心生成中的不对称Heck反应（AHR）中的应用。首次显示出对映选择性线性依赖于膦电子密度。通过改变R（2）或R（3）取代基来改变配体碱性，会逆转面部选择性。

  DOI：

  10.1021/ol0340179
• 作为产物：
  描述：

  N-((1S,2S)-2-Amino-1-tert-butyl-3,3-dimethyl-butyl)-4-methyl-benzenesulfonamide 在 sodium naphthalenide 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 (S,S)-1,2-di-tert-butylethane-1,2-diamine
  参考文献：
  名称：

  Enantioselective synthesis of (1S,2S)-1,2-di-tert-butyl and (1R,2R)-1,2-di-(1-adamantyl)ethylenediamines

  摘要：

  An enantioselective synthesis of sterically congested 1,2-di-tert-butyl and 1,2-di-(1-adamantyl)ethylenediamines has been developed. Thus, diastereomerically pure trans-1-apocamphanecarbonyl-4,5-dimethoxy-2-imidazolidinones 6 and 7 were successfully prepared by optical resolution of (+/-)-trans-4,5-dimethoxy-2-imidazolidinone using apocamphanecarbonyl chloride (MAC-Cl) followed by stereospecific and stepwise substitution of the dimethoxyl groups using tert-butyl or 1-adamantyl cuprates to provide (4S,5S)-4,5-di-tert-butyl and (4R,5R)-4,5-di-(1-adamantyl)-2-imidazolidinones 12 and 15, respectively. Furthermore, N-acetyl 4,5-di-tert-butyl and 4,5-di-(1-adamantyl)-2-imidazolidinones 16a,b were enantioselectively deacetylated using a catalytic oxazaborolidine system to provide enantiopure 1-p-tolylsulfonyl-4,5-di-tert-butyl-2-imidazolidinones 12 and 19 and 1-p-tolylsulfonyl-4,5-di-(1-adamantyl)-2-imidazolidinones 18 and 20, respectively. Finally, N-p-tolylsulfonyl-2-imidazolidinones 12 and 15 were treated with 30equiv of Ba(OH)(2.)8H(2)O to achieve ring cleavage and to provide (1S,2S)-1,2-di-tert-butylethylenediamine 3 and (1R,2R)-1,2-di(1-adamantyl)ethylenediamine 4. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.164

文献信息

• Chiral Bis(N-sulfonylamino)phosphine- and TADDOL-Phosphite-Oxazoline Ligands: Synthesis and Application in Asymmetric Catalysis
  作者：Robert Hilgraf、Andreas Pfaltz

  DOI：10.1002/adsc.200404168

  日期：2005.1

  has been prepared, containing a chiral oxazoline ring and as a second chiral unit a bis(N-sulfonylamino)phosphine group embedded in a diazaphospholidine ring or a cyclic phosphite group derived from TADDOL. These modular ligands are readily synthesized from chiral amino alcohols and chiral 1,2-diamines or TADDOLs. Palladium and iridium complexes derived from these ligands were found to be efficient catalysts

  制备了一系列N，P-配体，其包含手性恶唑啉环和嵌入在二氮磷吡啶环中的双（N-磺酰基氨基）膦基或衍生自TADDOL的环状亚磷酸酯基作为第二手性单元。这些模块化配体易于从手性氨基醇和手性1,2-二胺或TADDOLs合成。发现衍生自这些配体的钯和铱配合物分别是对映选择性烯丙基烷基化和烯烃氢化的有效催化剂。
• A New, Short, and Stereocontrolled Synthesis of <i>C</i>₂-Symmetric 1,2-Diamines
  作者：Rajender Vemula、Nathan C. Wilde、Rajendar Goreti、E. J. Corey

  DOI：10.1021/acs.orglett.7b01768

  日期：2017.7.21

  reaction of ammonia, glyoxal hydrate, and cyclohexanone. It is a very useful precursor for the diastereocontrolled synthesis of many C2-symmetric 1,2-diamines, a class which is important for the generation of a variety of C2-symmetric reagents and catalysts for enantioselective synthesis.

  通过氨，乙二醛水合物和环己酮的反应，可以高效，简单地制备出以前未知的5-螺环己基异咪唑。对于许多C 2对称的1,2-二胺的非对映控制合成而言，它是非常有用的前体，这一类对于产生各种C 2对称的试剂和对映选择性合成的催化剂很重要。
• Probing Electronic Effects in the Asymmetric Heck Reaction with the BIPI Ligands
  作者：Carl A. Busacca、Danja Grossbach、Regina C. So、Erin M. O'Brie、Earl M. Spinelli

  DOI：10.1021/ol0340179

  日期：2003.2.1

  new BIPI ligands are phosphinoimidazolines that can be electronically tuned in three different ligand regions to explore electronic effects in asymmetric catalysis. Their application to the asymmetric Heck reaction (AHR) in the creation of a chiral quaternary center is described. Enantioselectivity is shown for the first time to depend linearly on phosphine electron density. Changing the ligand basicity

  [结构：见正文]新的BIPI配体是膦基咪唑啉，可在三个不同的配体区域进行电子调节，以探索不对称催化中的电子效应。描述了它们在手性四元中心生成中的不对称Heck反应（AHR）中的应用。首次显示出对映选择性线性依赖于膦电子密度。通过改变R（2）或R（3）取代基来改变配体碱性，会逆转面部选择性。
• Enantioselective synthesis of (1S,2S)-1,2-di-tert-butyl and (1R,2R)-1,2-di-(1-adamantyl)ethylenediamines
  作者：Alaa A.-M. Abdel-Aziz、Serry A.A. El Bialy、Fatma E. Goda、Takehisa Kunieda

  DOI：10.1016/j.tetlet.2004.08.164

  日期：2004.10

  An enantioselective synthesis of sterically congested 1,2-di-tert-butyl and 1,2-di-(1-adamantyl)ethylenediamines has been developed. Thus, diastereomerically pure trans-1-apocamphanecarbonyl-4,5-dimethoxy-2-imidazolidinones 6 and 7 were successfully prepared by optical resolution of (+/-)-trans-4,5-dimethoxy-2-imidazolidinone using apocamphanecarbonyl chloride (MAC-Cl) followed by stereospecific and stepwise substitution of the dimethoxyl groups using tert-butyl or 1-adamantyl cuprates to provide (4S,5S)-4,5-di-tert-butyl and (4R,5R)-4,5-di-(1-adamantyl)-2-imidazolidinones 12 and 15, respectively. Furthermore, N-acetyl 4,5-di-tert-butyl and 4,5-di-(1-adamantyl)-2-imidazolidinones 16a,b were enantioselectively deacetylated using a catalytic oxazaborolidine system to provide enantiopure 1-p-tolylsulfonyl-4,5-di-tert-butyl-2-imidazolidinones 12 and 19 and 1-p-tolylsulfonyl-4,5-di-(1-adamantyl)-2-imidazolidinones 18 and 20, respectively. Finally, N-p-tolylsulfonyl-2-imidazolidinones 12 and 15 were treated with 30equiv of Ba(OH)(2.)8H(2)O to achieve ring cleavage and to provide (1S,2S)-1,2-di-tert-butylethylenediamine 3 and (1R,2R)-1,2-di(1-adamantyl)ethylenediamine 4. (C) 2004 Elsevier Ltd. All rights reserved.